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While this Jamaican spring break favorite is great for party animals, it can also be surprisingly low key – if you want. Montego Bay has excellent duty-free shopping, vibrant nightlife, and calm waters. Browse the local handicrafts at the open-air Harbour Street market, or the "hip strip" shops of Gloucester Avenue. The underwater crevices of Widowmaker’s Cave offer an intricate diving experience. Float serenely down the Martha Brae River on a bamboo raft and let your troubles melt away under the sun.